Neil Simon, renowned for his light-hearted domestic comedies, found immense success at the box office, with twenty-one of his twenty-six plays produced over three decades achieving commercial triumph. His ability to attract audiences translated into a substantial financial fortune. However, the critical reception of his works often told a different story. Detractors pointed out Simon's apparent indifference to formal experimentation, criticizing him for churning out comedies filled with predictable gags. Despite widespread popularity, his plays were often dismissed as lacking depth, leading to a reputation that deterred many regional theaters from staging his works.

However, the critical landscape began to shift with Simon's Brighton Beach trilogy, which introduced themes more complex than critics had anticipated, particularly the exploration of parent-child conflicts in Broadway Bound. This trilogy invited a reevaluation of Simon's earlier works, encouraging some critics to acknowledge the more profound undercurrents beneath their comedic surfaces.

With Lost in Yonkers, Simon achieved a new level of critical acclaim. The play won him a Tony Award and a Drama Desk Award, and contrary to his own predictions, it also earned the 1991 Pulitzer Prize for Drama. Critics lauded it as perhaps his finest work, a dark comedy that drew humor from painful familial tensions. Many praised the authenticity with which Simon depicted family conflicts, particularly highlighting the emotionally charged scenes between Bella and her mother.

Despite these accolades, not all feedback was entirely positive. Some critics took issue with the play's pacing, pointing out the slow exposition of the family dynamics at the outset. Others questioned the play's resolution, arguing that its optimistic ending felt contrived and at odds with the play's otherwise intense narrative. Mimi Kramer of The New Yorker notably maintained a wholly negative stance, criticizing the play for a perceived lack of honesty and authenticity. Nevertheless, Lost in Yonkers has found a place in the repertoires of regional and collegiate theater groups, defying Simon's concerns about its reception.

The mixed critical reception of Lost in Yonkers can be partly attributed to Simon's immense popularity. Success in the commercial realm often breeds skepticism among critics, who may equate popularity with a lack of artistic merit. Early reviews were divided; Stefan Kanfer, writing for the New Leader, likened Simon’s method to that of a craftsman rather than an artist, while Mimi Kramer criticized the play's characterizations and thematic coherence.

Nevertheless, Simon's work found its champions. David Richards, writing for The New York Times Magazine, hailed Simon as "the last Broadway playwright," suggesting a unique standing among his contemporaries, even while questioning the playwright's autobiographical denials. James S. Torrens, in America, affirmed the play's ability to resonate emotionally with audiences.

Over the ensuing years, the perception of Simon's oeuvre and Lost in Yonkers in particular underwent a transformation. J. Ellen Gainor noted a strategic shift in critical reception following the Pulitzer Prize win, with critics increasingly offering consistent praise. By 2002, as Susan Koprince articulated, Lost in Yonkers had solidified its status as both a critical and popular success, marking a high point in Simon's illustrious career.